#------------------------------------------------------------------------------ #$Date: 2015-04-02 14:22:18 +0300 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/05/2010571.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2010571 loop_ _publ_author_name 'Oguz, Umut' 'McLaughlin, Mark L.' 'Fronczek, Frank R.' _publ_section_title ; 2-Nitro-N,N-bis(2-nitrophenylthio)benzenesulfonamide ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first e27 _journal_page_last e28 _journal_paper_doi 10.1107/S0108270199016121 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C18 H12 N4 O8 S3' _chemical_formula_sum 'C18 H12 N4 O8 S3' _chemical_formula_weight 508.51 _chemical_name_systematic ; 2-nitro-N,N-bis(2-nitrophenylthio)benzenesulfonamide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _cell_angle_alpha 90 _cell_angle_beta 90.63(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.670(3) _cell_length_b 19.766(5) _cell_length_c 13.759(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 100 _cell_measurement_theta_max 18.1 _cell_measurement_theta_min 10.5 _cell_volume 2085.8(11) _computing_cell_refinement 'CAD-4 Express (Enraf-Nonius, 1994)' _computing_data_collection 'CAD-4 Express (Enraf-Nonius, 1994)' _computing_data_reduction 'MolEN (Fair, 1990)' _computing_publication_material 'CIFGEN in MolEN (Fair, 1990)' _computing_structure_refinement 'LSFM in MolEN (Fair, 1990)' _computing_structure_solution 'SIR (Burla et al., 1989)' _diffrn_ambient_temperature 100 _diffrn_measurement_device 'Enraf-Nonius CAD-4 (with Oxford Cryostream)' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type Mo-K\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .018 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 5118 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 2.5 _diffrn_standards_decay_% 2.9 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .412 _exptl_absorpt_correction_T_max .882 _exptl_absorpt_correction_T_min .835 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.619 _exptl_crystal_density_method none _exptl_crystal_description prism _exptl_crystal_F_000 1040 _exptl_crystal_size_max .50 _exptl_crystal_size_mid .33 _exptl_crystal_size_min .32 _refine_diff_density_max .62 _refine_diff_density_min -.37 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.320 _refine_ls_goodness_of_fit_ref 1.483 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 298 _refine_ls_number_reflns 4775 _refine_ls_number_restraints 0 _refine_ls_R_factor_all .062 _refine_ls_R_factor_gt .038 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 4Fo^2^/[\s^2^(Fo^2^) + 0.0004Fo^4^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .081 _refine_ls_wR_factor_ref .040 _reflns_number_gt 3426 _reflns_number_total 4775 _reflns_threshold_expression I>3\s(I) _[local]_cod_data_source_file qb0136.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_atom_site_thermal_displace_type' tag value 'Uij' was replaced with 'Uani' value 33 times. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'w = 4Fo^2^/[\s^2^(Fo^2^) + 0.0004Fo^4^]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 4Fo^2^/[\s^2^(Fo^2^) + 0.0004Fo^4^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2010571 _cod_database_fobs_code 2010571 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol S1 .0167(2) .0188(2) .0185(2) -.0015(2) -.0045(2) .0007(2) S S2 .0147(2) .0239(3) .0185(2) -.0020(2) -.0013(2) -.0044(2) S S3 .0159(2) .0199(2) .0180(2) -.0027(2) -.0013(2) .0002(2) S O1 .0159(7) .0239(8) .0306(8) .0008(7) -.0033(6) -.0014(7) O O2 .0278(8) .0264(8) .0183(7) -.0038(7) -.0073(6) .0027(7) O O3 .0470(10) .0309(9) .0215(8) -.0100(8) .0045(8) .0072(7) O O4 .0391(9) .0244(8) .0252(8) -.0015(8) .0065(7) -.0051(7) O O5 .0319(9) .0255(8) .0345(9) .0042(7) -.0008(7) -.0117(8) O O6 .0182(7) .0338(9) .0212(7) -.0012(7) -.0005(6) -.0033(7) O O7 .0366(9) .0440(10) .0174(7) .0080(9) .0003(7) .0038(8) O O8 .0223(8) .0288(8) .0267(8) -.0049(7) .0011(7) .0049(7) O N1 .0209(9) .0185(9) .0156(8) .0006(8) -.0018(7) -.0002(7) N N2 .0206(9) .0310(10) .0174(9) -.0035(9) .0006(7) .0006(8) N N3 .0211(9) .0270(10) .0189(9) .0028(8) -.0044(7) -.0007(8) N N4 .0270(10) .0201(9) .0204(9) .0052(8) -.0006(8) .0040(8) N C1 .0180(10) .0127(9) .0180(10) -.0006(8) -.0054(8) .0021(8) C C2 .0230(10) .0160(10) .0148(9) .0012(9) -.0016(8) .0017(9) C C3 .0200(10) .0190(10) .0230(10) -.0029(9) -.0028(9) .0029(9) C C4 .0230(10) .0210(10) .0220(10) -.0046(9) -.0077(9) .0004(9) C C5 .0280(10) .0190(10) .0144(9) .0010(10) -.0017(9) .0013(9) C C6 .0180(10) .0150(10) .0200(10) .0011(9) -.0002(9) .0022(9) C C7 .0150(10) .0190(10) .0180(10) -.0029(9) -.0040(8) .0019(9) C C8 .0170(10) .0200(10) .0190(10) .0026(9) -.0011(8) .0025(9) C C9 .0240(10) .0200(10) .0330(10) -.0010(10) -.0060(10) -.0060(10) C C10 .0190(10) .0290(10) .0490(10) -.0050(10) -.0060(10) -.0080(10) C C11 .0150(10) .0330(10) .0450(10) .0010(10) .0020(10) -.0080(10) C C12 .0200(10) .0220(10) .0270(10) -.0010(10) -.0006(9) -.0070(10) C C13 .0190(10) .0140(10) .0190(10) .0010(9) -.0036(8) .0002(9) C C14 .0200(10) .0140(10) .0210(10) .0028(9) -.0013(9) .0013(9) C C15 .0310(10) .0250(10) .0220(10) .0020(10) -.0070(10) .0030(10) C C16 .0200(10) .0330(10) .0360(10) -.0010(10) -.0120(10) .0040(10) C C17 .0170(10) .0330(10) .0330(10) .0020(10) .0010(10) .0050(10) C C18 .0200(10) .0250(10) .0190(10) .0030(10) -.0005(9) .0018(9) C loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol S1 .66531(7) .29449(3) .70051(4) .0180(2) Uani ? ? S S2 .54977(7) .42605(3) .77802(4) .0186(2) Uani ? ? S S3 .64999(7) .40948(3) .56947(4) .0179(2) Uani ? ? S O1 .8301(2) .28243(8) .65720(10) .0227(8) Uani ? ? O O2 .6404(2) .28076(8) .80100(10) .0238(8) Uani ? ? O O3 .2660(2) .20796(9) .82480(10) .0316(9) Uani ? ? O O4 .2594(2) .31341(8) .78240(10) .0289(9) Uani ? ? O O5 .5973(2) .60058(8) .95510(10) .0304(9) Uani ? ? O O6 .4663(2) .51013(8) .90190(10) .0235(8) Uani ? ? O O7 .5594(2) .41081(9) .26520(10) .0303(9) Uani ? ? O O8 .7003(2) .44192(8) .39540(10) .0258(8) Uani ? ? O N1 .6122(2) .37610(9) .68280(10) .0182(9) Uani ? ? N N2 .2878(2) .25370(10) .76620(10) .0223(9) Uani ? ? N N3 .5973(2) .54610(10) .91290(10) .0220(9) Uani ? ? N N4 .5683(2) .41973(9) .35330(10) .0223(9) Uani ? ? N C1 .5069(3) .25140(10) .63090(10) .0160(10) Uani ? ? C C2 .3425(3) .23490(10) .66680(10) .0180(10) Uani ? ? C C3 .2195(3) .20240(10) .6098(2) .0200(10) Uani ? ? C C4 .2586(3) .18800(10) .5139(2) .0220(10) Uani ? ? C C5 .4208(3) .20400(10) .47700(10) .0200(10) Uani ? ? C C6 .5455(3) .23490(10) .5354(2) .0180(10) Uani ? ? C C7 .7515(3) .46480(10) .81010(10) .0180(10) Uani ? ? C C8 .7571(3) .52070(10) .8719(2) .0190(10) Uani ? ? C C9 .9113(3) .55430(10) .8951(2) .0250(10) Uani ? ? C C10 1.0635(3) .53240(10) .8561(2) .0300(10) Uani ? ? C C11 1.0631(3) .47670(10) .7954(2) .0280(10) Uani ? ? C C12 .9106(3) .44310(10) .7724(2) .0230(10) Uani ? ? C C13 .4407(3) .40060(10) .5136(2) .0170(10) Uani ? ? C C14 .4195(3) .40450(10) .4126(2) .0180(10) Uani ? ? C C15 .2593(3) .39440(10) .3671(2) .0260(10) Uani ? ? C C16 .1151(3) .38140(10) .4217(2) .0290(10) Uani ? ? C C17 .1320(3) .37780(10) .5217(2) .0270(10) Uani ? ? C C18 .2921(3) .38730(10) .5671(2) .0220(10) Uani ? ? C H3 .1098 .1900 .6359 .0267 Uiso calc C3 H H4 .1736 .1671 .4732 .0289 Uiso calc C4 H H5 .4466 .1937 .4113 .0268 Uiso calc C5 H H6 .6575 .2447 .5102 .0236 Uiso calc C6 H H9 .9104 .5921 .9377 .0331 Uiso calc C9 H H10 1.1696 .5552 .8705 .0421 Uiso calc C10 H H11 1.1699 .4612 .7690 .0401 Uiso calc C11 H H12 .9137 .4048 .7306 .0302 Uiso calc C12 H H15 .2498 .3965 .2983 .0340 Uiso calc C15 H H16 .0045 .3750 .3913 .0389 Uiso calc C16 H H17 .0322 .3687 .5599 .0362 Uiso calc C17 H H18 .3005 .3846 .6359 .0283 Uiso calc C18 H loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C .002 .002 International_Tables_Vol_IV_Table_2.3.1 H .000 .000 International_Tables_Vol_IV_Table_2.3.1 N .004 .003 International_Tables_Vol_IV_Table_2.3.1 O .008 .006 International_Tables_Vol_IV_Table_2.3.1 S .110 .124 International_Tables_Vol_IV_Table_2.3.1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 3 0 -5 -3 0 -5 1 -17 0 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O1 S1 O2 120.26(9) O1 S1 N1 108.37(9) O1 S1 C1 107.60(10) O2 S1 N1 106.76(9) O2 S1 C1 109.70(10) N1 S1 C1 102.74(9) N1 S2 C7 100.85(9) N1 S3 C13 101.14(9) S1 N1 S2 120.80(10) S1 N1 S3 117.10(10) S2 N1 S3 121.60(10) O3 N2 O4 124.6(2) O3 N2 C2 117.7(2) O4 N2 C2 117.6(2) O5 N3 O6 124.0(2) O5 N3 C8 119.7(2) O6 N3 C8 116.3(2) O7 N4 O8 123.3(2) O7 N4 C14 119.6(2) O8 N4 C14 117.1(2) S1 C1 C2 122.8(2) S1 C1 C6 118.4(2) C2 C1 C6 118.8(2) N2 C2 C1 122.2(2) N2 C2 C3 116.3(2) C1 C2 C3 121.5(2) C2 C3 C4 118.9(2) C2 C3 H3 120.6 C4 C3 H3 120.6 C3 C4 C5 120.4(2) C3 C4 H4 119.8 C5 C4 H4 119.8 C4 C5 C6 120.4(2) C4 C5 H5 119.8 C6 C5 H5 119.8 C1 C6 C5 120.0(2) C1 C6 H6 120.0 C5 C6 H6 120.0 S2 C7 C8 120.9(2) S2 C7 C12 122.4(2) C8 C7 C12 116.6(2) N3 C8 C7 119.6(2) N3 C8 C9 117.8(2) C7 C8 C9 122.6(2) C8 C9 C10 119.2(2) C8 C9 H9 120.4 C10 C9 H9 120.4 C9 C10 C11 119.7(2) C9 C10 H10 120.1 C11 C10 H10 120.1 C10 C11 C12 121.3(2) C10 C11 H11 119.4 C12 C11 H11 119.4 C7 C12 C11 120.5(2) C7 C12 H12 119.7 C11 C12 H12 119.7 S3 C13 C14 121.2(2) S3 C13 C18 122.1(2) C14 C13 C18 116.7(2) N4 C14 C13 119.3(2) N4 C14 C15 118.5(2) C13 C14 C15 122.2(2) C14 C15 C16 119.7(2) C14 C15 H15 120.1 C16 C15 H15 120.1 C15 C16 C17 119.3(2) C15 C16 H16 120.4 C17 C16 H16 120.4 C16 C17 C18 121.0(2) C16 C17 H17 119.5 C18 C17 H17 119.5 C13 C18 C17 121.1(2) C13 C18 H18 119.5 C17 C18 H18 119.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 O1 . . 1.423(2) ? S1 O2 . . 1.424(2) ? S1 N1 . . 1.681(2) ? S1 C1 . . 1.758(2) ? S2 N1 . . 1.712(2) ? S2 C7 . . 1.777(2) ? S3 N1 . . 1.721(2) ? S3 C13 . . 1.781(2) ? O3 N2 . . 1.224(2) ? O4 N2 . . 1.220(3) ? O5 N3 . . 1.224(2) ? O6 N3 . . 1.239(2) ? O7 N4 . . 1.225(2) ? O8 N4 . . 1.241(2) ? N2 C2 . . 1.482(3) ? N3 C8 . . 1.445(3) ? N4 C14 . . 1.443(3) ? C1 C2 . . 1.397(3) ? C1 C6 . . 1.389(3) ? C2 C3 . . 1.380(3) ? C3 C4 . . 1.386(3) ? C3 H3 . . .95 ? C4 C5 . . 1.386(3) ? C4 H4 . . .95 ? C5 C6 . . 1.384(3) ? C5 H5 . . .95 ? C6 H6 . . .95 ? C7 C8 . . 1.395(3) ? C7 C12 . . 1.399(3) ? C8 C9 . . 1.391(3) ? C9 C10 . . 1.361(3) ? C9 H9 . . .95 ? C10 C11 . . 1.382(4) ? C10 H10 . . .95 ? C11 C12 . . 1.378(3) ? C11 H11 . . .95 ? C12 H12 . . .95 ? C13 C14 . . 1.399(3) ? C13 C18 . . 1.389(3) ? C14 C15 . . 1.387(3) ? C15 C16 . . 1.369(3) ? C15 H15 . . .95 ? C16 C17 . . 1.382(3) ? C16 H16 . . .95 ? C17 C18 . . 1.384(3) ? C17 H17 . . .95 ? C18 H18 . . .95 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion O1 S1 N1 S2 -128.90(10) O1 S1 N1 S3 42.90(10) O2 S1 N1 S2 1.90(10) O2 S1 N1 S3 173.80(10) C1 S1 N1 S2 117.40(10) C1 S1 N1 S3 -70.80(10) O1 S1 C1 C2 160.1(2) O1 S1 C1 C6 -21.7(2) O2 S1 C1 C2 27.6(2) O2 S1 C1 C6 -154.2(2) N1 S1 C1 C2 -85.6(2) N1 S1 C1 C6 92.6(2) C7 S2 N1 S1 94.90(10) C7 S2 N1 S3 -76.60(10) N1 S2 C7 C8 166.4(2) N1 S2 C7 C12 -10.9(2) C13 S3 N1 S1 96.30(10) C13 S3 N1 S2 -91.90(10) N1 S3 C13 C14 -162.7(2) N1 S3 C13 C18 14.9(2) O3 N2 C2 C1 -112.6(2) O3 N2 C2 C3 69.8(3) O4 N2 C2 C1 70.9(3) O4 N2 C2 C3 -106.6(2) O5 N3 C8 C7 -169.2(2) O5 N3 C8 C9 9.8(3) O6 N3 C8 C7 10.4(3) O6 N3 C8 C9 -170.6(2) O7 N4 C14 C13 166.4(2) O7 N4 C14 C15 -14.0(3) O8 N4 C14 C13 -14.0(3) O8 N4 C14 C15 165.7(2) S1 C1 C2 N2 1.2(3) S1 C1 C2 C3 178.6(2) C6 C1 C2 N2 -177.0(2) C6 C1 C2 C3 .4(3) S1 C1 C6 C5 -176.8(2) C2 C1 C6 C5 1.5(3) N2 C2 C3 C4 175.3(2) C1 C2 C3 C4 -2.3(3) C2 C3 C4 C5 2.2(3) C3 C4 C5 C6 -.4(3) C4 C5 C6 C1 -1.5(3) S2 C7 C8 N3 2.1(3) S2 C7 C8 C9 -176.9(2) C12 C7 C8 N3 179.6(2) C12 C7 C8 C9 .6(3) S2 C7 C12 C11 176.7(2) C8 C7 C12 C11 -.7(3) N3 C8 C9 C10 -178.8(2) C7 C8 C9 C10 .3(3) C8 C9 C10 C11 -.9(4) C9 C10 C11 C12 .8(4) C10 C11 C12 C7 .1(4) S3 C13 C14 N4 -3.6(3) S3 C13 C14 C15 176.7(2) C18 C13 C14 N4 178.6(2) C18 C13 C14 C15 -1.0(3) S3 C13 C18 C17 -177.3(2) C14 C13 C18 C17 .5(3) N4 C14 C15 C16 -178.5(2) C13 C14 C15 C16 1.2(3) C14 C15 C16 C17 -.7(4) C15 C16 C17 C18 .1(4) C16 C17 C18 C13 .0(5)